Acetic Acid → HCID 14700045, compound

HRID 1650193Notes

Reaction equation

HRID 1650193 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8].[H-].[Na+].[C:12]1([C:22]([C:24]2[C:31]([Cl:32])=[CH:30][C:27]([CH2:28]Br)=[CH:26][C:25]=2[Cl:33])=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.C(O)(=O)C>CN(C)C=O.O>[NH2:1][C:2]1[N:6]([CH2:28][C:27]2[CH:26]=[C:25]([Cl:33])[C:24]([C:22]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)=[O:23])=[C:31]([Cl:32])[CH:30]=2)[N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 14700030HCID 14700030, compoundHCID 178513860HCID 178513860, compound

Product 1

HCID 14700045HCID 14700045, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 5-amino-l,2,3-triazole-4-carboxamide (364 mg, 2.86 mmol) in 5 ml of dry dimethylformamide was treated with 50 % sodium hydride dispersion in mineral oil (137 mg, 2.86 mmol). The reaction mixture was warmed to 45° C. and then stirred for 45 minutes. A solution of 4-(1-naphthoyl)-3,5-dichlorobenzyl bromide (0.98 g, 2.49 mmol) in 5 ml of dry dimethylformamide was added. The reaction mixture was heated at 45° C. for an additional 20 minutes and then stirred at ambient temperatures for 1 hour. The mixture was slowly added to 100 ml of water containing two drops of glacial acetic acid. The precipitate was collected by filtration and thoroughly washed with water. The solid was dissolved in methylene chloride and washed with brine and dried with anhydrous sodium sulfate. Evaporation of the solvent afforded 1.11 g of crude product which was purified by column chromatography on silica gel (3g methanol in methylene chloride) to give 0.365 g of 5-Amino-1-[4-(l-naphthoyl)-3,5-dichlorobenzyl]1,2,3-triazole-4-carboxamide and 0.46 g of an isomer of undefined regiochemistry.

Workup

  1. temperatureThe reaction mixture was heated at 45° C. for an additional 20 minutes
  2. stirringstirred at ambient temperatures for 1 hour
  3. filtrationThe precipitate was collected by filtration
  4. washthoroughly washed with water
  5. dissolutionThe solid was dissolved in methylene chloride
  6. washwashed with brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. customEvaporation of the solvent
  9. customafforded 1.11 g of crude product which
  10. customwas purified by column chromatography on silica gel (3g methanol in methylene chloride)

Sources & evidence

ORD record
ord-1ad8f04e80ad443993d87264755f50c9
Source dataset
uspto-grants-1990_05
Patent number
US04923885

Reaction notes

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